Undertaker lost his first match... or rather was counted out in the Surivor Series, although his team techincally won with DiBiase as sole survivor.... the Gobbldeygooker? That was OUR loss...and shame.
The "winning debut" was always easy during the Hogan era, because of jobbers. They'd beat Mike Starr or the like in seconds in their first match whoever they were and only very rarely, like a deliberate DQ or similar and then face a "name" at the PPV. But push was very much "one up, one down" in those days. They always started with guys on the way down and replaced them in the spot till they got to the mid card or upper card and then were positioned for a main event here and there. It was formulaic but you didn't really get "shock wins" too often.
More recently, they've gone back to the strong debut but some still do lose right after, Rusev debuted in a Rumble, anyone who does loses unless they win the whole thing but was then unbeaten for a year. Someone more "recent" like Neville also wrestled on RAW last year in the run up to Takeover and scored the pin over Breeze, so whenever Breeze does "debut" he lost his first match.
Of course WWE likes to think they "control" this, they can retcon and try to convince you someone won when they lost or won a title when no tourney took place for it.
Cena wasn't a jobber though, that's the misconception, but he was a rookie... like Neville is now he was pitched right at top guys immediately, cos he lost matches to them he was labelled a jobber but he instantly rose to the mid card rather than the usual amble around the lower card. He bypassed about 6 months of build in 2 matches with Angle and Jericho after all if he was a jobber, Jericho wouldn't have insisted on taking the loss to him. Neville is in a similar situation right now, won some, lost some but all to top top guys... and without spoilers, it looks like he is following the same path, right into the midcard title hunt.